Private Pickleball Lessons & Coaches in Holliston, MA

Coming from a background in ping pong, Charley quickly became fond of pickleball during the tail end of COVID, gathering people from his church to play. Years later, as a World Pickleball Tour National Champion (January 2025) with a 4.5+ DUPR rating, Charley has reached the pinnacle of amateur competitive pickleball. With a Massachusetts teaching license and two years of coaching experience, he is passionate about helping players of all skill levels and age groups refine their techniques and develop a deeper love for the game. Additionally, he leads a weekly group and provides extra repetition with a ball-serving machine to maximize practice and improvement. Let’s take your pickleball game to the next level—let me know when you’re ready to get started!

"Charley was patient, knowledgeable and fun!

With two years of coaching experience and competing as a sponsored athlete, I bring a unique perspective to pickleball instruction. My passion is helping players of all levels unlock their full potential on the court. Let's elevate your game! Please message me about any inquiries, the more time I have to prepare the better as I also play in tournaments and so my schedule can fill up quick!

"Ayann really honed in on form and gave great tips for defensive strategy. Excited to my next 2 lessons- I think Ayann is really going to help me elevate passed 3.5

Peter embarked on a pickleball journey in July 2023 following a period of personal challenges. Introduced to the sport by a friend, pickleball quickly became a cornerstone of Peter's life, facilitating a remarkable 37-pound weight loss and reigniting a sense of passion and purpose. With a strong foundation in tennis, soccer, and ping pong, Peter seamlessly transitioned to pickleball, now leveraging this experience to help newcomers jumpstart their own love affair with the sport, promoting health, happiness, and community along the way.

"Great opportunity to sharpen my skills!

I love pickleball and the community it’s given me. Having learned from incredible mentors, I’m ready to pay it forward. A former 4-year HS tennis player, I’ve since competed in APA tournaments across all formats. My coaching is collaborative yet direct—I focus on technical skills to sharpen strengths and fix weaknesses. I offer flexible teaching tailored to what works best for you, always balancing improvement with genuine fun. All levels are welcome—let’s get on the court and level up!

Michael, based in Haverhill, MA, is a dedicated pickleball coach passionate about teaching across the North Shore of Massachusetts and Southern New Hampshire. With experience coaching players of diverse skill levels, he has helped students prepare for the Special Olympics, facilitated corporate team-building events, and guided individuals in improving their DUPR ratings. Michael specializes in coaching beginners to upper-intermediate players, focusing on skill development and a deeper understanding of the game, ensuring every session is both effective and enjoyable.

"I wanted to specifically work on resets and moving up to the kitchen at the right time and the lesson with Mike was really helpful. He was patient and the drills were excellent.

As a passionate pickleball enthusiast and experienced tennis coach, I bring deep understanding of strategy, technique, and player development to the game. With years of coaching high-performance tennis players, my transition to pickleball was a natural evolution - one fueled by a love for competition, community and continuous learning. A major emphasis will be placed on placing the trainee on a path of self discovery for developing the student's ability to solve problems independently.

"Very knowledgable, emphasized technique and form, made the most of our 1hr intro lesson.

If you are thinking about learning to play the fastest growing sport in the nation, but are hesitant to begin, read this short bio of our most popular Rhode Island instructor, Coach Phyl. Her experience and coaching style can help to ease your concerns. Hello and welcome! I’m Coach Phyl, and I am so glad you’re here. Let me tell you a little about why I love to work with beginning pickleball players. Pickleball is life, and I mean that literally. I took up the sport just as the Covid pandemic was shifting into high gear. It was the one thing I could do, despite my advanced age, while lockdown was beginning to happen all around me. It got me off the couch and moving, which I believe saved me from losing my mind, my passion for life, and my muscles, such as they are. It was kismet. I quickly recognized how similar the movements and strategies were to a game called Ace King Queen that I had played as a child. I loved and missed that game. Pickleball felt almost like finding it again. I fell in love with it immediately, not only for the game itself, but also for the social void it filled. Pickleball has brought many wonderful people into my life while providing me with a fun way to stay active during my “golden” years. I am filled with gratitude for all that it gives me, and I want to share these benefits with as many people as I can. We will have fun while you learn and practice new drills and skills. Pickleball is a multi-tiered sport that can be played by just about anyone. There is no better way to learn the basics than through in-person coaching. My teaching style is relaxed and non-confrontational. You will learn the rules of the game, proper warm-up techniques, paddle basics, a variety of strokes, serving options, targeting, timing, and the importance of drilling, with a few advanced strategies thrown in for good measure. As I like to say, just do it! There's no time like the present, so join me. See you on the court! Speaking of courts… While I am willing to travel to other courts, I encourage you to choose the courts at the John H. Chafee Sports Complex at 450 Hope Road in Western Cranston. These courts are well maintained and easy to get to. I love playing there, and I think you will, too. That said, if the weather calls for rain or otherwise is not in a cooperative mood (think wind, intense heat, snow, etc.), then a good choice would be the private indoor court at Open Table.

"Phyllis was very nice and patient. Also very methodical and thorough in her approach in teaching the rules. Great experience with her! But I don't think this sport is for me at this time. I am very grateful for getting the opportunity to learn from Phyllis!

I love the friendly environment that comes with playing pickleball, and I strongly believe that it is one of the most unique sports, due to its ability to be learned quickly without much previous experience. I’m extremely patient, can work with individuals at any skill level, and can tailor lessons to individual needs/goals. Most importantly, I love pickleball and bring this passion to any and all pickleball-related events. If you’re a beginner or have never even touched a pickleball paddle, within a short amount of time you’ll be able to rally and start winning points. If you’re more advanced, you’ll perfect you’re serve, spin, and net game. All ages and skill levels welcome!

"I found the serve practice to be especially valuable during the lesson with Daisy. It helped me focus on an important part of the game and improved my confidence on the court. If you want to sharpen your pickleball skills, I recommend giving Daisy’s lessons a try. You won’t be disappointed!

I am a retired businessman who ran my company for 35 years. I have played and coached basketball, golf and now pickleball. I coached youth sports when my kids were younger and coached them for 8+ years on town teams. I am an avid pickleball player who mainly works with adults learning and teaching the game to them.

Ignite your passion for pickleball! With 25 years of coaching experience, honed by competing as a college athlete, I offer personalized guidance to elevate your game. My expertise ensures you'll achieve your goals while enjoying every moment on the court.